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Phosphorus, Sulfur, and Silicon and the Related Elements Volume 192, 2017 - Issue 2: 27th International Symposium on Organic Chemistry of Sulfur (ISOCS-27)
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Original Articles

Reaction of 2-alkylidene-3,1-benzoxathiin-4-ones with nitrones

Masao ShimizuNational Institute of Advanced Industrial Science and Technology (AIST), Tsukuba, Ibaraki, JapanCorrespondence[email protected]
,
Masaki YamanakaDepartment of Pure and Applied Chemistry, Faculty of Science and Technology, University of Science (RIKADAI), Chiba, Japan
,
Koujiro KuritaDepartment of Pure and Applied Chemistry, Faculty of Science and Technology, University of Science (RIKADAI), Chiba, Japan
,
Shinji TanakaNational Institute of Advanced Industrial Science and Technology (AIST), Tsukuba, Ibaraki, Japan
,
Wataru AndoNational Institute of Advanced Industrial Science and Technology (AIST), Tsukuba, Ibaraki, Japan
&
Norio SakaiDepartment of Pure and Applied Chemistry, Faculty of Science and Technology, University of Science (RIKADAI), Chiba, Japan
Pages 249-251 | Received 27 Oct 2016, Accepted 28 Oct 2016, Published online: 14 Nov 2016
 
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GRAPHICAL ABSTRACT

ABSTRACT

2-Methylene-3,1-benzoxathiin-4-ones reacted with nitrones at methylene moieties of 3,1-benzoxathiine rings to yield spiro 1,3-dipolar cycloadducts. The benzoxathiin-4-one rings easily occurred ring opening reaction with NaOSiMe3 and isoxazolidin-5-one derivatives were obtained in good yields. As a result, 2-methylene-3,1-benzoxathiin-4-ones can be used as a ketene equivalent.

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